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- 12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?What is the stereochemical configuration of the enantiomer of (2S, 4R)-2, 4-octanediol? (A diol is a compound with two —OH groups.)Identify the relationship between the following pair of structures by describing them as represting enantiomers, diastereomers, constitutional isomers or two molecules of the same compounds (a) (c) H H₂C H F Br Oll F CH3 Br H and Br. CH3 H and Fumus (d) H H X-X=-= CH3 H CH3 (b) Br HO CHO and -OH H C(O)CH3 and HO H- CHO -H -OH C(O)CH3
- 5. Given the following structure: (a) Draw all the stereoisomers; CH2 OH (b) Identify all of the enantiomeric and diastereomeric pairs; (c) Assign R or S configuration at each asymmetric carbon for each structure. Justify your assignments for the original structure (above).Consider the reaction between (1S,3S)-1-chloro-3-methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. -SH C NaOH Draw only the organic product. Select /// Draw Rings More C H S Erase:Identify the relationship between the following pair of structures by describing them as represting enantiomers, diastereomers, constitutional isomers or two molecules of the same compounds (a) (c) H CH3 Br. CH3 Br f-f and Filmas H H CH3 H F Oll H CHO Br X-X ²=-= -OH HO and and H Br H- F C(O)CH, H (b) CH3 (d) H- and HO CHO -H -OH C(O)CH3
- 5) Consider each pair of structures below; indicate which one the species are [1] Constitutional isomers: [2] Enantiomers: [3] Diastereomers: [4] Identical: (B) H,N. HO. (A) FOH OH (D) HO. (C) HO. NH2(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.8. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) H3C c) CH3 Br H. CH3 Br Br CH3 H. CI Holl H Cill Cl- CH3 Br H. CI CH3 HO. H. H3C Cl H3C- H- H. CH3 Cl a) b) c) 9. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) c) CH2CH3 NH2 HO CH3 H3C. CH3 Cl HO H;C CH2CH3 F. F H;C. CI H H,N -CH3 CH3 NH2 H3C Br H2N C1 H3C CH3 CH3 H;CH,C- Cl F H. H Br CH,CH3 CH3 a) b) c)
- Determine the absolute Configuration (2 ors) of the Stereogenic centre in (i) and (ii) HO # CH ₂ Br (ii) HO compounds CHO H 1 CH₂2₂ CH ₂The structure of A is shown below. HO 3 -CH2CH=CH2 A (i) Predict the possible number of stereoisomers A can have. (ii) Draw the 3D structure of the (25, 3R, 5S) enantiomer showing its correct stereochemistry. (iii) Calculate the specific rotation of each enantiomer in a mixture containing 10 mL (0.10 M) of (2S, 3R, 55) enantiomer and 30 mL (0.10 M) of (2R, 3S, 5R) enantiomer. Given the specific rotation of the mixture = +4.8°.For the following pairs of compounds, indicate the relationship (identical compounds, enantiomers, diastereomers, or constitutional isomers). The same answer can be used more than once. (b) H (a) H HO COME MeO2C OH NH2 NH2 H2N H -NH2 H. MeO2C H HO' `CO,Me H Но, H (c) CH2CH3 (d) CH3 Br Br -CH2CH3 Br H- Br, H EH H EH но— H;C CH3 H3C+Br H- -Br CH3 H CH3